Tetrahydrofuran → 5-Bromo-2-phenyl-4-thiazolecarboxylic acid

HRID 1182675노트

반응식

HRID 1182675 반응식
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([OH:14])=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.[Li]CCCC.[Br:25]Br>C1CCCCC1>[Br:25][C:9]1[S:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:11][C:10]=1[C:12]([OH:14])=[O:13]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 24408BromineHCID 1389282-Phenyl-4-carboxythiazoleHCID 178418339Butyllithium

생성물 1

HCID 667697155-Bromo-2-phenyl-4-thiazolecarboxylic acid

시약·촉매·용매 1

HCID 8078Cyclohexane용매

실험 절차

To a solution of 2-phenyl-1,3-thiazole-4-carboxylic acid (3.2 g) in abs. THF (190 mL) was added at 78° C. over 10 min n-BuLi (25 mL, 1.6M in hexanes). After addition, Br2 (1.3 mL) in cyclohexane (7.4 mL) was added over 10 min. The reaction mixture was allowed to warm up to RT and was stirred at this temperature for 3 h. The reaction mixture was then cooled to 0° C., carefully quenched with HCl (1M, 32 mL) and extracted with EtOAc (2×). The combined org. phases were washed with aq. sodium thiosulfate (20%), dried over MgSO4 and evaporated to dryness to give 4.5 g of the desired product. The crude was used without further purification.

후처리

  1. additionwas added over 10 min
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. customcarefully quenched with HCl (1M, 32 mL)
  4. extractionextracted with EtOAc (2×)
  5. washphases were washed with aq. sodium thiosulfate (20%)
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-8d0f46c900804d8785f0fd842c6b5a03
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664203B2

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